The total synthesis of plagiochin D, a macrocyclic bis(bibenzyl) compound isolated from the liverwort plagiochila acanthophylla, has been accomplished. Closure of the key 16‐membered ring, which contained biphenyl ether and biaryl units, was achieved in good yield by an intramolecular SNAr reaction. The Suzuki and Wittig protocols proved to be powerful tools for the construction of a linear precursor that was crucial for ring cyclization.

Three novel energetic compounds were prepared from the common precursor 1-fluoro-2,4-dinitrobenzene by using nucleophilic aromatic substitution as a key step with pentaerythritol, pentaerythritoltrinitrate, or glycidol. The thermal stability of 3-(2,4-dinitrophenoxy)-2,2-bis[(nitrooxy)methyl]propyl nitrate was assessed by differential scanning calorimetry and its X-ray structure was determined. In light of the success in using 2,4-dinitroanisole as an additive in explosive formulations, some of the analogous compounds prepared in the present study may be considered as suitable materials for diverse composite energetic material formulations.

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